Lewis acid assisted annelation of trimethylsilyl enol ethers of 1-acetylcyclohexenes with α,β-unsaturated carbonyl compounds to give substituted 2-decalones; synthesis of (±)-ε-cadinene

Abstract

The trimethylsilyl enol ethers of 1-acetylcyclohexenes undergo a Lewis-acid-assisted one-pot annelation reaction with α,β-unsaturated carbonyl compounds to produce 5-substituted 2-decalones; the application of this reaction has enabled a synthesis of (±)-ε-cadinene (12).